Rolling with Resilience (RwR) provides a springboard for developing strategies that build strengths and supports to foster developmental assets in children and youth (Benson, Scales, & Roehlkepartain, 2011). In Circle of Courage terms, resilience is strengthened by opportunities for Belonging, Mastery, Independence, and Generosity (Brendtro, Brokenleg, & Van Bockern, 2002). Participants describe this training experience as different from other parenting courses that focus on problems and consequence-based discipline. Instead, they learn practical, positive strategies which apply to daily life in home and community. This experiential learning can be useful for all who work with youth--as well as for young people themselves. Also, organizations that embrace the Circle of Courage philosophy find RwR effective either as an induction or a refresher for those who have completed Response Ability Pathways and other Circle of Courage trainings. The overarching goal of RwR is to understand and apply the Circle of Courage to real-world challenges faced by children and families. This is achieved through opportunities for reflection and activities that translate each of the four Circle of Courage principles (Belonging, Mastery, Independence, and Generosity) into action. The RwR training package caters to a wide range of learning styles. Resources include a PowerPoint presentation with facilitators' notes and a guidebook for participants. This article describes each of the three modules of experiential learning through which RwR participants progress in order to understand, explore, and apply the Circle of Courage to their life situations.